We've continually raised the price on our product as we grow and add features. It was nerve wracking at first, but now are confident enough in our product that we feel good standing behind our pricing.
We are targeting larger, more stable customers, and have historically found the ones that say our pricing is too expensive are the ones that require much more support and maintenance. Have no issue seeing them go to cheaper competitors - while our target clients don't bat an eye at our pricing (which is still probably too low for that segment).